Resorcinol → m-(p-Toluidino)phenol

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of p-toluidine (13.4 g, 126.2 mol), resorcinol (10 g, 90.8 mmol) and p-toluidine HCl (1.3 g, 9.0 mmol) was heated at 160° C. for 48 h with an oil bath. After cooling to room temperature, the reaction mixture in 500 mL of diethyl ether was treated with 2N NaOH to give precipitated materials and filtered under reduced pressure. The collected solid was treated with glacial acetic acid until completely dissolved, and the solution was extracted with diethyl ether (2×200 mL). The ether layer was washed with water (2×150 mL), dried over MgSO4, and concentrated under reduced pressure to give a dark-brown oil, which was purified by flash column chromatography using EtOAc/hexane (40:60). The resulting oil was crystallized from CH2Cl2/hexane to yield 13.4 g (74%) of the title compound as a dark brown solid. Mp 86-88° C. (lit 91° C. )

Provenance & Evidence